Karsil

Karsil
Names
	Preferred IUPAC name N-(3,4-Dichlorophenyl)-2-methylpentanamide
	Other names (2RS)-3′,4′-Dichloro-2-methylpentananilide; (RS)-3′,4′-Dichloro-2-methylvaleranilide; N-(3,4-Dichlorophenyl)-2-methylpentanamide; NIA 4562;
Identifiers
CAS Number	2533-89-3;
3D model (JSmol)	Interactive image;
ChemSpider	517504;
PubChem CID	595317;
UNII	7WAZ49QYN0;
CompTox Dashboard (EPA)	DTXSID40871872 ;
	InChI InChI=1S/C12H15Cl2NO/c1-3-4-8(2)12(16)15-9-5-6-10(13)11(14)7-9/h5-8H,3-4H2,1-2H3,(H,15,16) Key: VUNCGGHZBFQRPB-UHFFFAOYSA-N;
	SMILES CCCC(C)C(=O)NC1=CC(=C(C=C1)Cl)Cl;
Properties
Chemical formula	C12H15Cl2NO
Molar mass	260.16 g·mol−1
Density	1222 kg/m3
Melting point	106 °C (223 °F; 379 K)
Boiling point	396 °C (745 °F; 669 K)
Vapor pressure	1.79 nmHg
Hazards
Flash point	193
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Karsil (also called erlüjixiancaoan) is an acylanilide herbicide, similar to propanil. It is potent against annual grasses and broadleaved weeds in celery, and a strong inhibitor of photosynthesis. It is approved for use in China.

When degraded by bacteria, karsil becomes 3,4-dichloroaniline and 3,3',4,4,'-tetrachloroazobenzene. Karsil is theorised to form hydrogen bonds with the protein of an enzyme involved in the oxidation of water, creating its herbicidal potential, similar to diuron and atrazine.

Karsil has been manufactured by Niagara Chemical Division. If ingested, activated charcoal absorbs it. Karsil is ten times as active as atrazine at the chloroplast level.

References

1 2 "erlujixiancaoan data sheet". bcpcpesticidecompendium.org.
1 2 3 4 5 "Buy erlujixiancaoan from HANGZHOU JHECHEM CO LTD". ECHEMI.
1 2 Sharabi, Nagim El-Din; Bordeleau, Lucien M. (September 1969). "Biochemical Decomposition of the Herbicide N-(3,4-Dichlorophenyl)-2-Methylpentanamide and Related Compounds". Applied Microbiology. 18 (3): 369–375. doi:10.1128/am.18.3.369-375.1969. PMC 377987. PMID 5373674.
↑ van Overbeek, J. (1962). "Physiological Responses of Plants to Herbicides". Weeds. 10 (3): 170–174. doi:10.2307/4040775. JSTOR 4040775.
↑ Wallnöfer, P. R.; Safe, S.; Hutzinger, O. (1 July 1972). "Die hydroxylation des herbizids karsil (N-(3,4-Dichlorophenyl)-2-methylpentanamid) durch Rhizopusjaponicus". Chemosphere. 1 (4): 155–158. doi:10.1016/0045-6535(72)90019-7.
↑ "Analytical reference standards and supplemental data for pesticides and other organic compounds". nepis.epa.gov. January 1981.
↑ Masatoshi, Ghobara; Duke, Stephen O.; Takematsu, Tetsuo (August 26, 1987). "MT-5950, a New Anilide Herbicide, Inhibits PSII at a Site that Slightly Overlaps the Triazine Binding Site". Agric. Biol. Chem.: 465–472. Retrieved 15 March 2025.

[bcpc-1] 1 2 "erlujixiancaoan data sheet". bcpcpesticidecompendium.org.

[echemi-2] 1 2 3 4 5 "Buy erlujixiancaoan from HANGZHOU JHECHEM CO LTD". ECHEMI.

[s1969-3] 1 2 Sharabi, Nagim El-Din; Bordeleau, Lucien M. (September 1969). "Biochemical Decomposition of the Herbicide N-(3,4-Dichlorophenyl)-2-Methylpentanamide and Related Compounds". Applied Microbiology. 18 (3): 369–375. doi:10.1128/am.18.3.369-375.1969. PMC 377987. PMID 5373674.

[4] van Overbeek, J. (1962). "Physiological Responses of Plants to Herbicides". Weeds. 10 (3): 170–174. doi:10.2307/4040775. JSTOR 4040775.

[5] Wallnöfer, P. R.; Safe, S.; Hutzinger, O. (1 July 1972). "Die hydroxylation des herbizids karsil (N-(3,4-Dichlorophenyl)-2-methylpentanamid) durch Rhizopusjaponicus". Chemosphere. 1 (4): 155–158. doi:10.1016/0045-6535(72)90019-7.

[6] "Analytical reference standards and supplemental data for pesticides and other organic compounds". nepis.epa.gov. January 1981.

[7] Masatoshi, Ghobara; Duke, Stephen O.; Takematsu, Tetsuo (August 26, 1987). "MT-5950, a New Anilide Herbicide, Inhibits PSII at a Site that Slightly Overlaps the Triazine Binding Site". Agric. Biol. Chem.: 465–472. Retrieved 15 March 2025.